NO128962B - - Google Patents

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Info

Publication number: NO128962B
Authority: NO; Norway
Prior art keywords: group; compounds; carbon atoms; general formula; stands
Prior art date: 1968-02-26

Application number

NO00603/69A

Other languages

English (en)

Norwegian (no)

Inventor

H Ott

Original Assignee

Sandoz Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1968-02-26

Filing date

1969-02-14

Publication date

1974-02-04

1969-02-14 Application filed by Sandoz Ag filed Critical Sandoz Ag

1974-02-04 Publication of NO128962B publication Critical patent/NO128962B/no

Links

150000001875 compounds Chemical class 0.000 claims description 52
125000004432 carbon atom Chemical group C* 0.000 claims description 39
238000000034 method Methods 0.000 claims description 26
-1 hydroxy- Chemical class 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 24
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
229910052794 bromium Inorganic materials 0.000 claims description 15
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
239000011737 fluorine Substances 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
229910052727 yttrium Inorganic materials 0.000 claims description 3
239000012345 acetylating agent Substances 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
238000005903 acid hydrolysis reaction Methods 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 34
239000000243 solution Substances 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
238000001953 recrystallisation Methods 0.000 description 26
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
239000012074 organic phase Substances 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 14
239000002904 solvent Substances 0.000 description 13
239000007858 starting material Substances 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000003960 organic solvent Substances 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
238000009835 boiling Methods 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
238000010992 reflux Methods 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
239000011592 zinc chloride Substances 0.000 description 7
235000005074 zinc chloride Nutrition 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
150000003388 sodium compounds Chemical class 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000725 suspension Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 3
MZPDVYDLHYUTQS-UHFFFAOYSA-N (2-amino-5-methylphenyl)-phenylmethanone Chemical compound CC1=CC=C(N)C(C(=O)C=2C=CC=CC=2)=C1 MZPDVYDLHYUTQS-UHFFFAOYSA-N 0.000 description 2
MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 2
HRPHZUAPQWJPCZ-UHFFFAOYSA-N (2-chloro-5-nitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C(=O)C=2C=CC=CC=2)=C1 HRPHZUAPQWJPCZ-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
AWAVJMREBRKGOY-UHFFFAOYSA-N [2-(ethylamino)-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound CCNC1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 AWAVJMREBRKGOY-UHFFFAOYSA-N 0.000 description 2
VLEZORDMPZZAFA-UHFFFAOYSA-N [2-(ethylamino)-5-nitrophenyl]-phenylmethanone Chemical compound CCNC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 VLEZORDMPZZAFA-UHFFFAOYSA-N 0.000 description 2
QMHAHUAQAJVBIW-UHFFFAOYSA-N [methyl(sulfamoyl)amino]methane Chemical compound CN(C)S(N)(=O)=O QMHAHUAQAJVBIW-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
230000001754 anti-pyretic effect Effects 0.000 description 2
239000002221 antipyretic Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
229940111759 benzophenone-2 Drugs 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
239000002178 crystalline material Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000000605 extraction Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
239000000155 melt Substances 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
GZYBWMKOQXCCHC-UHFFFAOYSA-N (2-amino-5-methylsulfanylphenyl)-phenylmethanone Chemical compound CSC1=CC=C(N)C(C(=O)C=2C=CC=CC=2)=C1 GZYBWMKOQXCCHC-UHFFFAOYSA-N 0.000 description 1
UFBFCUNAXFUILT-UHFFFAOYSA-N 1-phenylquinazolin-2-one Chemical compound O=C1N=CC2=CC=CC=C2N1C1=CC=CC=C1 UFBFCUNAXFUILT-UHFFFAOYSA-N 0.000 description 1
OKDGPOCKHMGDQY-UHFFFAOYSA-N 3,4-dihydropyrrol-2-one Chemical compound O=C1CCC=N1 OKDGPOCKHMGDQY-UHFFFAOYSA-N 0.000 description 1
FHUBTSLLILWICW-UHFFFAOYSA-N 4-phenyl-1h-quinazolin-2-one Chemical compound C12=CC=CC=C2NC(=O)N=C1C1=CC=CC=C1 FHUBTSLLILWICW-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
DILPRJPRBYHSDX-UHFFFAOYSA-N CCC(C(N)=CC([N+]([O-])=O)=C1)=C1C(C1=CC=CC=C1)=O Chemical compound CCC(C(N)=CC([N+]([O-])=O)=C1)=C1C(C1=CC=CC=C1)=O DILPRJPRBYHSDX-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
241000206575 Chondrus crispus Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QHDJJBSLUFDASY-UHFFFAOYSA-N [2-chloro-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound FC(F)(F)C1=CC=C(Cl)C(C(=O)C=2C=CC=CC=2)=C1 QHDJJBSLUFDASY-UHFFFAOYSA-N 0.000 description 1
KIYLOYFQTWNSLH-UHFFFAOYSA-N [5-nitro-2-(propan-2-ylamino)phenyl]-phenylmethanone Chemical compound CC(C)NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 KIYLOYFQTWNSLH-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001339 alkali metal compounds Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
244000243234 giant cane Species 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003112 potassium compounds Chemical class 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
KEAYESYHFKHZAL-BJUDXGSMSA-N sodium-22 Chemical compound [22Na] KEAYESYHFKHZAL-BJUDXGSMSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
230000007306 turnover Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO00603/69A 1968-02-26 1969-02-14 NO128962B (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US70793268A	1968-02-26	1968-02-26
US74180468A	1968-07-01	1968-07-01

Publications (1)

Publication Number	Publication Date
NO128962B true NO128962B (da)	1974-02-04

Family

ID=27107992

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO00603/69A NO128962B (da)	1968-02-26	1969-02-14

Country Status (10)

Country	Link
BG (4)	BG17597A3 (da)
DK (3)	DK128007B (da)
ES (1)	ES364005A1 (da)
IE (1)	IE33434B1 (da)
IL (1)	IL31683A (da)
NO (1)	NO128962B (da)
OA (1)	OA03389A (da)
PL (2)	PL79534B1 (da)
RO (2)	RO57857A (da)
SE (1)	SE353911B (da)

1968
- 1968-10-28 PL PL1968129788A patent/PL79534B1/pl unknown
1969
- 1969-02-14 NO NO00603/69A patent/NO128962B/no unknown
- 1969-02-17 DK DK86669AA patent/DK128007B/da unknown
- 1969-02-19 SE SE02281/69A patent/SE353911B/xx unknown
- 1969-02-24 IL IL31683A patent/IL31683A/xx unknown
- 1969-02-24 ES ES364005A patent/ES364005A1/es not_active Expired
- 1969-02-24 PL PL1969131919A patent/PL70441B1/pl unknown
- 1969-02-24 IE IE238/69A patent/IE33434B1/xx unknown
- 1969-02-25 BG BG013126A patent/BG17597A3/xx unknown
- 1969-02-25 BG BG011741A patent/BG17592A3/xx unknown
- 1969-02-25 RO RO64032A patent/RO57857A/ro unknown
- 1969-02-25 BG BG013123A patent/BG17596A3/xx unknown
- 1969-02-25 BG BG013122A patent/BG17595A3/xx unknown
- 1969-02-25 RO RO59192A patent/RO55407A/ro unknown
- 1969-02-26 OA OA53522A patent/OA03389A/xx unknown
1970
- 1970-03-04 DK DK107870AA patent/DK127187B/da unknown
- 1970-03-04 DK DK108170AA patent/DK128564B/da unknown

Also Published As

Publication number	Publication date
SE353911B (da)	1973-02-19
RO57857A (da)	1975-02-15
BG17595A3 (bg)	1973-11-10
DK128007B (da)	1974-02-18
IE33434B1 (en)	1974-06-26
ES364005A1 (es)	1971-02-16
OA03389A (fr)	1970-12-15
IL31683A (en)	1974-09-10
PL79534B1 (da)	1975-06-30
RO55407A (da)	1974-03-01
DK128564B (da)	1974-05-27
DK127187B (da)	1973-10-01
PL70441B1 (da)	1974-02-28
BG17592A3 (bg)	1973-11-10
BG17596A3 (bg)	1973-11-10
IL31683A0 (en)	1969-04-30
BG17597A3 (bg)	1973-11-10
IE33434L (en)	1969-08-26

Publication	Publication Date	Title
CA1041108A (en)	1978-10-24	Antihistaminic imidazoles
EP0028834B1 (en)	1984-01-18	Imidazole-5-acetic acid derivatives, their production and use
NO177304B (no)	1995-05-15	Analogifremgangsmåte for fremstilling av terapeutisk aktive benzimidazolderivater
NO124032B (da)	1972-02-21
GB2082580A (en)	1982-03-10	Tricyclic imidazole derivatives
NO851862L (no)	1985-11-13	Fremgangsmaate ved fremstilling av nye pyrrolobenzimidazoler
US3435049A (en)	1969-03-25	Nitroimidazole derivatives
NO822918L (no)	1983-03-01	Nye imidazokinazolinderivater.
NO764039L (da)	1977-06-06
KR860001338B1 (ko)	1986-09-15	4-아로일이미다졸-2-온의 제조방법
PL82659B1 (en)	1975-10-31	7-(imidazolinyl-(2)-amino)-indazoles[us3847934a]
HU203736B (en)	1991-09-30	Process for producing new thiouracil-derivatives and pharmaceutical compositions containing them
US3819627A (en)	1974-06-25	1-substituted-3,4-dihydro-2(1h)-quinazolinones
US3764600A (en)	1973-10-09	1-substituted-quinazoline-2(1h)-thiones
JPH0365349B2 (da)	1991-10-11
IE46279B1 (en)	1983-04-20	Sulphamoylbenzoic acids
US3390150A (en)	1968-06-25	Process for the preparation of 1-(beta-hydroxyethyl)-5-nitroimidazole-2-carboxylic acid gamma-lactone
EP0244352A2 (en)	1987-11-04	Pyrido[4,3-d]pyrimidine derivatives
IL32504A (en)	1973-06-29	Quinazoline-2(1h)-thione derivatives,their preparation and pharmaceutical preparations containing them
NO150281B (no)	1984-06-12	Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive 3,4,5,6-tetrahydro(1,3)thiazolo(3,4-a)isokinolinderivater
EP0052959B1 (en)	1986-01-29	Production of purine derivatives and intermediates therefor
NO157142B (no)	1987-10-19	6-fenyl-hydrazon-6,7,8,9-tetrahydro-11h-pyrido(2,1-b)kinazolin-11-oner.
US4467087A (en)	1984-08-21	1,2,4-Triazines
US3644392A (en)	1972-02-22	1-substituted-5-nitroimidazole-2-carboximidates
KR860001509B1 (ko)	1986-09-30	2-아미노-5(6)-치환된-벤즈이미다졸의 제조 방법